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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:54:13 UTC

Update Date

2021-09-26 23:17:46 UTC

HMDB ID

HMDB0259916

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Xanthenone-4-acetic acid

Description

2-(9-oxo-9H-xanthen-4-yl)acetic acid belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Based on a literature review very few articles have been published on 2-(9-oxo-9H-xanthen-4-yl)acetic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Xanthenone-4-acetic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Xanthenone-4-acetic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0259916
     RDKit          3D
Xanthenone-4-acetic acid
 29 31  0  0  0  0  0  0  0  0999 V2000
    3.7920    0.7254    1.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821    1.3450    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7555    2.6494    0.5727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6725    0.6378   -0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8833   -0.5791   -0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5173   -1.7962   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7899   -2.9320   -0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4532   -2.8143   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684   -1.5733   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200   -1.4751    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613   -2.5167    0.5927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0621   -0.2104    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -0.0778    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772    1.1804    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871    2.2555    0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587    2.1722   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958    0.8857   -0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281    0.7579   -0.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270   -0.4296   -0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234    3.0440    1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    1.3445   -1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792    0.3104   -1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5901   -1.8755   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2631   -3.9087   -0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1632   -3.6486    0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.9778    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0318    1.2665    0.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    3.2195    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2446    3.0209   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19  5  1  0
 19  9  2  0
 17 12  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END


  Mrv1533004241519562D          

 19 21  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259916

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1=CC=CC2=C1OC1=CC=CC=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O4/c16-13(17)8-9-4-3-6-11-14(18)10-5-1-2-7-12(10)19-15(9)11/h1-7H,8H2,(H,16,17)

> <INCHI_KEY>
ABGYSGBNWQSGJD-UHFFFAOYSA-N

> <FORMULA>
C15H10O4

> <MOLECULAR_WEIGHT>
254.241

> <EXACT_MASS>
254.057908802

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.206212617793728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(9-oxo-9H-xanthen-4-yl)acetic acid

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.5973885096666667

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.33970093990804

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7623073768978057

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
68.1239

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9-oxoxanthen-4-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259916
     RDKit          3D
Xanthenone-4-acetic acid
 29 31  0  0  0  0  0  0  0  0999 V2000
    3.7920    0.7254    1.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821    1.3450    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7555    2.6494    0.5727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6725    0.6378   -0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8833   -0.5791   -0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5173   -1.7962   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7899   -2.9320   -0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4532   -2.8143   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684   -1.5733   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200   -1.4751    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613   -2.5167    0.5927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0621   -0.2104    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -0.0778    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772    1.1804    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871    2.2555    0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587    2.1722   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958    0.8857   -0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281    0.7579   -0.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270   -0.4296   -0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234    3.0440    1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    1.3445   -1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792    0.3104   -1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5901   -1.8755   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2631   -3.9087   -0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1632   -3.6486    0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.9778    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0318    1.2665    0.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    3.2195    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2446    3.0209   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19  5  1  0
 19  9  2  0
 17 12  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9                                                       
CONECT   16   12   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0259916
HETATM    1  O1  UNL     1       3.792   0.725   1.144  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.082   1.345   0.270  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.755   2.649   0.573  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.672   0.638  -0.963  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.883  -0.579  -0.643  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.517  -1.796  -0.646  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.790  -2.932  -0.323  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.453  -2.814  -0.008  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.168  -1.573  -0.013  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.520  -1.475   0.303  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.161  -2.517   0.593  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.062  -0.210   0.272  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.402  -0.078   0.576  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.977   1.180   0.551  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.187   2.255   0.223  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.859   2.172  -0.084  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.296   0.886  -0.053  1.00  0.00           C  
HETATM   18  O4  UNL     1      -0.028   0.758  -0.344  1.00  0.00           O  
HETATM   19  C15 UNL     1       0.527  -0.430  -0.328  1.00  0.00           C  
HETATM   20  H1  UNL     1       2.723   3.044   1.509  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.107   1.344  -1.602  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.579   0.310  -1.529  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.590  -1.875  -0.899  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.263  -3.909  -0.318  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.163  -3.649   0.247  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.958  -0.978   0.831  1.00  0.00           H  
HETATM   27  H8  UNL     1      -5.032   1.266   0.793  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.677   3.219   0.213  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.245   3.021  -0.344  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6    6   19
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   25
CONECT    9   10   19   19
CONECT   10   11   11   12
CONECT   12   13   13   17
CONECT   13   14   26
CONECT   14   15   15   27
CONECT   15   16   28
CONECT   16   17   17   29
CONECT   17   18
CONECT   18   19
END

HMDB0259916
     RDKit          3D
Xanthenone-4-acetic acid
 29 31  0  0  0  0  0  0  0  0999 V2000
    3.7920    0.7254    1.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821    1.3450    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7555    2.6494    0.5727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6725    0.6378   -0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8833   -0.5791   -0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5173   -1.7962   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7899   -2.9320   -0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4532   -2.8143   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684   -1.5733   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200   -1.4751    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613   -2.5167    0.5927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0621   -0.2104    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -0.0778    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772    1.1804    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871    2.2555    0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587    2.1722   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958    0.8857   -0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281    0.7579   -0.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270   -0.4296   -0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234    3.0440    1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    1.3445   -1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792    0.3104   -1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5901   -1.8755   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2631   -3.9087   -0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1632   -3.6486    0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.9778    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0318    1.2665    0.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    3.2195    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2446    3.0209   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19  5  1  0
 19  9  2  0
 17 12  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(9-oxo-9H-Xanthen-4-yl)acetate	Generator
Xanthenone-4-acetate	Generator
XOAA	MeSH

Chemical Formula

C₁₅H₁₀O₄

Average Molecular Weight

254.241

Monoisotopic Molecular Weight

254.057908802

IUPAC Name

2-(9-oxo-9H-xanthen-4-yl)acetic acid

Traditional Name

(9-oxoxanthen-4-yl)acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC1=CC=CC2=C1OC1=CC=CC=C1C2=O

InChI Identifier

InChI=1S/C15H10O4/c16-13(17)8-9-4-3-6-11-14(18)10-5-1-2-7-12(10)19-15(9)11/h1-7H,8H2,(H,16,17)

InChI Key

ABGYSGBNWQSGJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.67	ALOGPS
logP	2.6	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.34	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.12 m³·mol⁻¹	ChemAxon
Polarizability	25.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	156.133	32859911
AllCCS	[M+H-H2O]+	152.18	32859911
AllCCS	[M+Na]+	160.867	32859911
AllCCS	[M+NH4]+	159.809	32859911
AllCCS	[M-H]-	158.453	32859911
AllCCS	[M+Na-2H]-	157.697	32859911
AllCCS	[M+HCOO]-	156.989	32859911
DeepCCS	[M+H]+	151.072	30932474
DeepCCS	[M-H]-	148.711	30932474
DeepCCS	[M-2H]-	181.774	30932474
DeepCCS	[M+Na]+	157.163	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.58 minutes	32390414
Predicted by Siyang on May 30, 2022	13.0801 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2127.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	411.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	240.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	300.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	374.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	558.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	102.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1124.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	479.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1347.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	326.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	357.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	229.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	17.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xanthenone-4-acetic acid	OC(=O)CC1=CC=CC2=C1OC1=CC=CC=C1C2=O	3455.8	Standard polar	33892256
Xanthenone-4-acetic acid	OC(=O)CC1=CC=CC2=C1OC1=CC=CC=C1C2=O	2236.0	Standard non polar	33892256
Xanthenone-4-acetic acid	OC(=O)CC1=CC=CC2=C1OC1=CC=CC=C1C2=O	2431.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthenone-4-acetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1290000000-f493ab73951f70c440fd	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthenone-4-acetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthenone-4-acetic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthenone-4-acetic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

142175

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Xanthenone-4-acetic acid (HMDB0259916)

MOL for HMDB0259916 (Xanthenone-4-acetic acid)

3D MOL for HMDB0259916 (Xanthenone-4-acetic acid)

3D SDF for HMDB0259916 (Xanthenone-4-acetic acid)

3D-SDF for HMDB0259916 (Xanthenone-4-acetic acid)

PDB for HMDB0259916 (Xanthenone-4-acetic acid)

3D PDB for HMDB0259916 (Xanthenone-4-acetic acid)

SMILES for HMDB0259916 (Xanthenone-4-acetic acid)

INCHI for HMDB0259916 (Xanthenone-4-acetic acid)

Structure for HMDB0259916 (Xanthenone-4-acetic acid)

3D Structure for HMDB0259916 (Xanthenone-4-acetic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra